A primary driver for pursuing the development of technology based adaptive tutoring is an attempt to replicate the effects of one-to-one tutoring with human tutors (Bloom, 1984). This paper situates the discussion of adaptive tutoring in the context of a theory-driven approach to the design of specific cognitive tools. Different methods exist to model individual differences in learning and performance as a precursor to adaptive tutoring (Lajoie, 2007). This paper describes how students interact with technology to solve medical problems and how they learn through interactions with simulated patient cases. Specific examples of medical models are provided that guide the design of technology enriched learning environment, including expert models, models of medical teams, and models of the culture of medicine.